Is there wildlife in Chilmark, MA?

As of early 2026, 100% of users say there's wildlife

Are there community events in Chilmark, MA?

As of early 2026, 100% of users say there are community events

Is a car needed in Chilmark, MA?

As of early 2026, 100% of users say car is needed

Are yards well-kept in Chilmark, MA?

As of early 2026, 100% of users say yards are well-kept

Are neighbors friendly in Chilmark, MA?

As of early 2026, 78% of users say neighbors are friendly

Is Chilmark, MA dog-friendly?

As of early 2026, 75% of users say it's dog friendly

Would people walk alone at night in Chilmark, MA?

As of early 2026, 75% of users say people would walk alone at night

Is parking easy in Chilmark, MA?

As of early 2026, 67% of users say parking is easy

Is Chilmark, MA quiet?

As of early 2026, 67% of users say it's quiet

Do residents of Chilmark, MA plan to stay at least 5 years?

As of early 2026, 60% of users say they plan to stay for at least 5 years

Does Chilmark, MA show holiday spirit?

As of early 2026, 43% of users say there's holiday spirit

Is Chilmark, MA walkable to restaurants?

As of early 2026, 33% of users say it's walkable to restaurants

OFF MARKET

$6,225,000

Last sold price

6 Beds
6 Baths
3,494 sqft (on 3.40 acres)

5 Shepherds Path, Chilmark, MA 02535

Currently Off Market - Sold Jan 24, 2017 for $6,225,000

Home Value

Learn more about this home's value by checking out the value of nearby homes.

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Distance	Price	Bed	Bath	Sqft	Status
4 Ocean View Farm Rd, Chilmark, MA 02535	0.06	$1,811,400	4	3	3,272	Off Market
4 Shepherds Path, Chilmark, MA 02535	0.06	$6,929,000	6	6	3,256	Off Market
1 Osprey Ln, Chilmark, MA 02535	0.07	-	5	6	3,168	Off Market
5 Ocean View Farm Rd, Chilmark, MA 02535	0.07	$2,642,000	3	2	1,540	Off Market
11 Ocean View Farm Rd, Chilmark, MA 02535	0.08	$3,646,900	5	3	2,300	Off Market
6 Kings Hwy W, Chilmark, MA 02535	0.09	$1,715,900	3	2	2,126	Off Market
98 KINGS HWY W, CHILMARK , MA 02535	0.11	-	-	-	-	Off Market
6 Ocean View Farm Rd, Chilmark, MA 02535	0.11	$2,540,500	3	2	1,152	Off Market
5 Half Inch Ln, Chilmark, MA 02535	0.11	-	7	5	3,616	Off Market
5 Osprey Ln, Chilmark, MA 02535	0.12	$5,285,400	3	2	1,952	Off Market
47-53 Kings Hwy W, Chilmark, MA 02535	0.13	-	-	-	-	Off Market
11 Osprey Ln, Chilmark, MA 02535	0.13	$4,596,900	5	4	3,181	Off Market
17 Doctors Creek Path, Chilmark, MA 02535	0.14	$922,500	2	1	640	Off Market
5 Redwing Ln, Chilmark, MA 02535	0.15	$1,297,600	4	2	1,540	Off Market
10 Kings Hwy W, Chilmark, MA 02535	0.15	-	7	4	3,728	Off Market
10 Kings Hwy, Chilmark, MA 02535	0.15	-	-	-	-	Off Market
14 Ocean View Farm Rd, Chilmark, MA 02535	0.16	$2,030,700	3	1.5	1,428	Off Market
18 Osprey Ln, Chilmark, MA 02535	0.17	-	7	9	7,831	Off Market
11 Half Inch Ln, Chilmark, MA 02535	0.17	-	6	5	3,434	Off Market
11 Tanglevine Rd, Chilmark, MA 02535	0.17	$1,938,700	5	3	1,963	Off Market

Local Information

Map ViewExplore the area around 5 Shepherds Path.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Apartment

Built in 1971

3.4 acre lot

3,494 sqft

About this House

This apartment is located at 5 Shepherds Path, Chilmark, MA. 5 Shepherds Path is in Chilmark, MA and in ZIP code 02535. This property has 6 bedrooms, 6 bathrooms and approximately 3,494 sqft of floor space. This property has a lot size of 3.40 acres and was built in 1971.

5 Shepherds Path, Chilmark, MA 02535 is a 6 bedroom, 6 bathroom, 3,494 sqft apartment built in 1971. It last sold for $6,225,000 on Jan 24, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $6,640/month.

Home Details for 5 Shepherds Path

Interior Features
Levels, Entrance, & Accessibility Stories: 2
Interior Details Number of Rooms: 12
Heating & Cooling Air Conditioning

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Other

Property Information
Year Built Year Built: 1971
Property Type / Style Property Type: ApartmentArchitecture: Contemporary

Community
Units in Building: 1

Lot Information
Lot Area: 3.40 acres

Price and Tax history

Date	Event	Price
Jan 24, 2017 Source: LINK #31560	Sold	$6,225,000
May 23, 1994 Source: N/A	Sold	$615,000

Year	Property tax	Tax assessment
2025	$23,596	$10,487,300

Additional Cost

Market trends in Chilmark

Last updated October 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

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Available listings

Sourced by Trulia Market Trends

Around this home

West Tisbury Elementary School
PK-8
Public
334 Students
Up-Island Regional School District
7/10
GreatSchools Rating
Parent Rating Average
Kids rule the school. No accountability. Bullying is not taken seriously.
Parent Review
2y ago
5 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chilmark

At least 2 Trulia users voted on each feature.

100 % Say there's wildlife
100 % Say there are community events
100 % Say car is needed
100 % Say yards are well-kept
78 % Say neighbors are friendly
75 % Say it's dog friendly
75 % Say people would walk alone at night
67 % Say parking is easy
67 % Say it's quiet
60 % Say they plan to stay for at least 5 years
43 % Say there's holiday spirit
33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.

Elaine V.
12y ago
"I work and live here, and have been in Real estate here for over 20 years, I would recommend it to anyone who needs to feel a sense of community and enjoys nature. A wonderful place to live!!"
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Apartments for Rent

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Off Market Homes Near 5 Shepherds Path

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SOLD
NOV 10, 2026
$3,650,000
6 bd
3.5 ba
3,070 sqft
30-40 Elias Ln,
West Tisbury, MA 02575
Tea Lane Associates
SOLD
NOV 6, 2026
$2,850,000
3 bd
3 ba
1,469 sqft
28 Black Point Road,
Chilmark, MA 02535
Island Real Estate
SOLD
OCT 21, 2026
$4,850,000
3 bd
2.5 ba
2,095 sqft
63 Putnam Rd,
Chilmark, MA 02535
Wendy Harman, Compass
SOLD
OCT 20, 2026
$3,625,000
4 bd
3.5 ba
3,702 sqft
7 Black Point Rd,
Chilmark, MA 02535
Tea Lane Associates
SOLD
OCT 14, 2026
$2,325,000
4 bd
3 ba
2,350 sqft
16 South Rd,
Chilmark, MA 02535
Vineyard Village Realty
SOLD
OCT 6, 2026
$4,550,000
4 bd
4.5 ba
6,162 sqft
205 South Rd,
Chilmark, MA 02535
Donnelly + Co
SOLD
OCT 2, 2026
$3,550,000
3 bd
2 ba
1,562 sqft
11 Greenhouse Ln,
Chilmark, MA 02535
LINK
SOLD
SEP 30, 2026
$1,650,000
5 bd
3 ba
2,552 sqft
10 Danls Way,
West Tisbury, MA 02575
Studio Realty
SOLD
SEP 28, 2026
$3,800,000
3 bd
4.5 ba
3,314 sqft
20 Edson Forrest Rd,
West Tisbury, MA 02575
Tea Lane Associates
SOLD
SEP 24, 2026
$7,000,000
2 bd
2 ba
2,250 sqft
26 Harbor Hill Rd,
Chilmark, MA 02535
Tea Lane Associates
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